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Chemical Compound Review

SureCN156767     4-phenylbut-3-enoic acid

Synonyms: AG-E-39791, ACMC-20ajfo, CTK1A7335, CTK1E6641, CTK8C5382, ...
 
 
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Disease relevance of NSC172584

 

High impact information on NSC172584

  • The olefinic compound 4-phenyl-3-butenoic acid (PBA) is the most potent irreversible, mechanism-based PHM inactivator known [4].
  • In addition, we report that the olefinic substrate analogues trans-benzoylacrylic acid and 4-phenyl-3-butenoic acid are potent time-dependent inactivators of PAM, with inactivation exhibiting the characteristics expected for mechanism-based inhibition [5].
  • Reversal of the transformed phenotype and inhibition of peptidylglycine alpha-monooxygenase in Ras-transformed cells by 4-phenyl-3-butenoic acid [1].
  • Furthermore, 4-phenyl-3-butenoic acid (PBA), an alpha-amidation enzyme inhibitor, significantly (P<0.05) inhibited the vasorelaxant responses to hAM-gly without any effect on the hAM-induced relaxation, suggesting the possible process of amidation in the rat aorta [6].
  • At 10(-5) M, the specific inhibitors of PAM (4-phenyl-3-butenoic acid; PBA) and PGL (5-acetamido-2,4-diketo-6-phenyl-hexanoic acid and its methyl ester) reduced NO basal release by 40, 34, and 45%, respectively [7].
 

Biological context of NSC172584

  • Pretreatment of the aortic strips with 4-phenyl-3-butenoic acid (PBA), an irreversible amidating enzyme inactivator, results in marked inhibition of the vasodilation activity induced by SP-Gly but not of that induced by SP itself [8].

References

  1. Reversal of the transformed phenotype and inhibition of peptidylglycine alpha-monooxygenase in Ras-transformed cells by 4-phenyl-3-butenoic acid. Sunman, J.A., Foster, M.S., Folse, S.L., May, S.W., Matesic, D.F. Mol. Carcinog. (2004) [Pubmed]
  2. Streptomyces koyangensis sp. nov., a novel actinomycete that produces 4-phenyl-3-butenoic acid. Lee, J.Y., Lee, J.Y., Jung, H.W., Hwang, B.K. Int. J. Syst. Evol. Microbiol. (2005) [Pubmed]
  3. Isolation and antifungal activity of 4-phenyl-3-butenoic acid from Streptomyces koyangensis strain VK-A60. Lee, J.Y., Lee, J.Y., Moon, S.S., Hwang, B.K. J. Agric. Food Chem. (2005) [Pubmed]
  4. Peptidylglycine-alpha-hydroxylating monooxygenase generates two hydroxylated products from its mechanism-based suicide substrate, 4-phenyl-3-butenoic acid. Driscoll, W.J., König, S., Fales, H.M., Pannell, L.K., Eipper, B.A., Mueller, G.P. Biochemistry (2000) [Pubmed]
  5. Novel substrates and inhibitors of peptidylglycine alpha-amidating monooxygenase. Katopodis, A.G., May, S.W. Biochemistry (1990) [Pubmed]
  6. Glycine-extended adrenomedullin exerts vasodilator effect through amidation in the rat aorta. Cao, Y.N., Kitamura, K., Ito, K., Kato, J., Hashida, S., Morishita, K., Eto, T. Regul. Pept. (2003) [Pubmed]
  7. Vascular and endothelial actions of inhibitors of substance P amidation. Abou-Mohamed, G.A., Huang, J., Oldham, C.D., Taylor, T.A., Jin, L., Caldwell, R.B., May, S.W., Caldwell, R.W. J. Cardiovasc. Pharmacol. (2000) [Pubmed]
  8. Amidative peptide processing and vascular function. Oldham, C.D., Li, C., Feng, J., Scott, R.O., Wang, W.Z., Moore, A.B., Girard, P.R., Huang, J., Caldwell, R.B., Caldwell, R.W., May, S.W. Am. J. Physiol. (1997) [Pubmed]
 
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